Nucleophilic Substitution of Hydrogen Facilitated by Quinone Methide Moieties in Benzo[cd]azulen-3-ones



: Alexandros Kiriazis, Ingo B. Aumüller, Ralica Arnaudova, Vanessa Brito, Tobias Rüffer, Heinrich Lang, Samuel M. Silvestre, Päivi J. Koskinen, Jari Yli-Kauhaluoma

Publisher: AMER CHEMICAL SOC

: 2017

: Organic Letters

: ORGANIC LETTERS

: ORG LETT

: 19

: 8

: 2030

: 2033

: 4

: 1523-7060

: 1523-7052

DOI: https://doi.org/10.1021/acs.orglett.7b00588(external)


The built-in o- and p-QM (QM = quinone methide) moieties in benzo[cd]azulen-3-ones account for an easy switch between the bridged 10 pi- and 6 pi-aromatic systems in organic synthesis. We report conjugate additions, oxidative nucleophilic substitutions of hydrogen, and reversible Michael additions under very mild conditions. In the presence of thiol nucleophiles, the protonated sigma(H)-adducts could be isolated and characterized. The typical preference for either the o- or p-QM moiety led to high regioselectivity. Furthermore, the inhibitory potency of the novel benzo[cd]azulenes against the human Pim-1 kinase was evaluated.



Last updated on 2024-26-11 at 22:44